CASUAL MONDAYS PODCAST

Welcome to Casual Mondays, the retirement podcast for those who’ve closed the office planner and opened the door to tomorrow. Whether you're planning for retirement or already made the transition, join us for conversations about what happens after you step away from the 9-to-5: from day one plans to shaping a second act that’s as fulfilling as it is flexible.Expect expert advice, inspiring stories, and actionable tips for designing a life that’s rich in experiences, purpose, and joy. Trade your desk for a deck chair. This is the retirement podcast for living your best life - every single day.

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The Podcast for Early Retirees (and those preparing to be!)

Welcome to Casual Mondays, the retirement podcast for those who’ve closed the office planner and opened the door to tomorrow. Whether you're planning for retirement or already made the transition, join us for conversations about what happens after you step away from the 9-to-5: from day one plans to shaping a second act that’s rich in experiences, purpose, and joy.

Expect expert advice, inspiring stories, and honest conversation about the good, bad, and all the in betweens of life in retirement.

Trade your desk for a deck chair. This is the retirement podcast for living your best life - every single day.

NOTE: This is not an investment advice podcast. Consult a Certified Financial Planner for investment advice.

Retired? Working towards retirement? Join the Casual Mondays Club!

Recent

Feb. 9, 2026

Creating Structure Without the 9-to-5

It's 10:47 on a Tuesday morning. You're still in your pajamas, scrolling your phone. You had vague plans—organize the garage, call a friend, hit the gym. But there's no meeting at 11. No deadline at noon. No boss wondering wh...

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Jan. 19, 2026

Finding Your Ikigai - Your Reason for Being

You've retired. You can fill every hour with activities—golf, volunteering, travel—and still feel empty. You're busier than when you worked, but something fundamental is missing. This episode introduces the Japanese concept o...

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Dec. 25, 2025

Who Am I Without A Business Card? The Identity Shift

"So, what do you do?"Three weeks after leaving my 25-year career in luxury hospitality, I froze at this simple question. According to Harvard Business School research, I'm far from alone—the retirement identity crisis is one of the most profound psychological challenges that nobody talks about.…

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Dec. 9, 2025

Welcome to Casual Mondays

Welcome to Casual Mondays, the retirement podcast for those who’ve closed the office planner and opened the door to tomorrow. Whether you're planning for retirement or already made the transition, join us for conversations ab...

Listen to the Episode

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Retirement Success Graph

Stress test your retirement plan against 100+ years of market data with Retirement Success Graph.

Secure by design, the Retirement Success Graph app brings advisor-level analysis to your device without ads, subscriptions, or privacy compromises. The fully-functional, free-for-life app provides 50 simultaneous Monte Carlo model runs to measure your retirement plan against decades of economic data.

Unlock Premium features with a one-time $4.99 purchase, including support for multiple withdrawal methods, social security strategies, model retirement income and windfalls, and compare results over 10,000 simultaneous model runs.

Recent Blog Posts

Feb. 5, 2026

The Cocktail Party Question That's About to Break Everyone

There’s a cocktail party question that’s been making people uncomfortable for generations: “So, what do you do?”For most of my adult life, I had a ready answer. Market Director for a luxury hotel brand. Creative work, …

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Feb. 2, 2026

Your Reason for Being Beyond the Paycheck: Discovering Ikigai in Retirement

You've filled your calendar. Golf on Tuesdays, volunteering on Wednesdays, lunch with old colleagues on Thursdays. You're busier now than when you were working, yet something fundamental feels missing. You're checking boxes but not finding meaning. …

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Jan. 7, 2026

Five Critical Steps to Future-Proof Your Retirement Plan in 2026

Your retirement plan needs more than the 4% rule. These five steps address what financial advisors won't tell you about early retirement in 2026.You've run the numbers. Maybe you've even paid a financial advisor to double-check them. The…

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About the Host

Kevin Donahue

Author. Podcast Host. Pilgrim Backpacker. Aspiring Racer.

With a 25+ year track record of driving revenue, creating and repositioning brands, and developing leaders, Kevin Donahue is regarded as one of the elite marketing strategists and sales leaders in the luxury hospitality industry. He left the industry in his early fifties to prioritize intentional time as a husband and father, a pilgrim backpacker, an author, a digital developer, and a podcast host.

In his "retirement era", Kevin serves on the College of Business Advisory Council at Florida Gulf Coast University and is pursuing new passions, including auto racing and mobile app development.

For more on Kevin's active projects, please visit KevinDonahue.com and ChezMerStudios.com

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The Podcast for Early Retirees (and those preparing to be!)

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About the Host